By the time we got together and bought our first house 2 years after she graduated (she was 24), she had enough money saved up to put down 20% on our house by herself and she is a school teacher making less than 40k per year.

We've been working with a broker and have seen some interesting prospects, and were originally drawn to Yale by the idea of buying a house that would be marketable to Yale undergrads or graduate students.

The thought was to start with cash as we have a mortgage thats pretty hefty on our house as well as student loans(ugh).

Make students colleagues, not customers

Now I've moved out (because of a random conversation with a coworker and her fiance who were looking for a place) and have been renting my former primary residence to them for the last 2 years, with plans to renovate the inlaw suite and rent that out again also.In the years I've been working here, I've heard from coworkers and neighbors about the high demand of the employees to live close to work (which also happens to be less than 10 min out from the university, as many of them are college/grad/doctoral students).

I collect VA benefits and I'm also a student so I do have money coming in, plus my wife is employed (one of her jobs pays cash, another issue).

Our real estate agent suggested we apply for a student housing permit a d off the property as a rental to Students.

My current thinking is to purchase a 2-3 bed home in the South Side flats/slopes to rent out to students and young professionals.

this is really a question of common sense - so you friend has to see what the market will pay - supply and demand - and there are often rent laws in Germany so he should check that out - he would probably do better renting thru an agent (Makler) they have just made rules on how much a Makler can charge as well - he might also list it on Craigslist if it is in an urban area or a place of student demand and he has someone to handle the on site things. 

Not trying to be your english teacher, but I don't want to invest with someone without basic communication skills.